Reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride

被引：1
|
作者：
Sadykov, E. Kh. [1 ]
Lobanova, N. A. [1 ]
Stankevich, V. K. [1 ]
机构：
[1] Russian Acad Sci, Siberian Branch, Favorskii Irkutsk Inst Chem, Ul Favorskogo 1, Irkutsk 664033, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 52卷 / 04期
关键词：
FLUORINE;
D O I：
10.1134/S1070428016040096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chemo- and stereoselectivity of the reaction of 1-[2-(vinyloxy)ethyl]-1H-pyrroles with trifluoroacetic anhydride have been studied. The reaction with an equimolar amount of trifluoroacetic anhydride chemoselectively involves the free alpha-position of the pyrrole ring with formation of the corresponding alpha-trifluoroacetylpyrroles. In the reaction with 2 equiv of trifluoroacetic anhydride, acylation of both alpha-position of the pyrrole ring and beta-position of the vinyloxy group leads to the formation of 1-(2-{[(1E)-4,4,4-trifluoro-3-oxobut-1-en-1-yl]oxy}ethyl)-2-trifluoroacetyl derivatives with high stereoselectivity.
引用
收藏
页码：533 / 537
页数：5
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